EP1610177B1 - Lichtempfindlicher harzfilm und daraus hergestellter ausgehärteter film - Google Patents
Lichtempfindlicher harzfilm und daraus hergestellter ausgehärteter film Download PDFInfo
- Publication number
- EP1610177B1 EP1610177B1 EP04723323A EP04723323A EP1610177B1 EP 1610177 B1 EP1610177 B1 EP 1610177B1 EP 04723323 A EP04723323 A EP 04723323A EP 04723323 A EP04723323 A EP 04723323A EP 1610177 B1 EP1610177 B1 EP 1610177B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- photosensitive resin
- acrylate
- resin film
- radiation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 84
- 239000011347 resin Substances 0.000 title claims abstract description 84
- 230000005855 radiation Effects 0.000 claims abstract description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 229920001577 copolymer Polymers 0.000 claims abstract description 60
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 35
- 238000000576 coating method Methods 0.000 claims abstract description 34
- 239000011248 coating agent Substances 0.000 claims abstract description 33
- 238000002834 transmittance Methods 0.000 claims abstract description 30
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 87
- -1 acrylic acid aliphatic ester Chemical class 0.000 claims description 43
- 239000000470 constituent Substances 0.000 claims description 40
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 12
- 125000003367 polycyclic group Chemical group 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 claims description 9
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 8
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 230000009477 glass transition Effects 0.000 claims description 7
- 238000000016 photochemical curing Methods 0.000 claims description 2
- 239000000758 substrate Substances 0.000 abstract description 25
- 230000015572 biosynthetic process Effects 0.000 abstract description 20
- 239000000203 mixture Substances 0.000 abstract description 8
- 239000003999 initiator Substances 0.000 abstract description 2
- 239000010408 film Substances 0.000 description 176
- 239000000243 solution Substances 0.000 description 29
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- 150000003254 radicals Chemical class 0.000 description 18
- 239000011342 resin composition Substances 0.000 description 16
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- 238000007747 plating Methods 0.000 description 15
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- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 14
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- 238000011161 development Methods 0.000 description 11
- 230000018109 developmental process Effects 0.000 description 11
- 238000000034 method Methods 0.000 description 9
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
- 238000001723 curing Methods 0.000 description 8
- 238000009713 electroplating Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 150000005846 sugar alcohols Polymers 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229940116333 ethyl lactate Drugs 0.000 description 5
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 5
- 229910052737 gold Inorganic materials 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000010453 quartz Substances 0.000 description 5
- 229910000679 solder Inorganic materials 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000059 patterning Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 239000013065 commercial product Substances 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
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- 238000012719 thermal polymerization Methods 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
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- PMOWTIHVNWZYFI-UHFFFAOYSA-N o-Coumaric acid Natural products OC(=O)C=CC1=CC=CC=C1O PMOWTIHVNWZYFI-UHFFFAOYSA-N 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- QJVXKWHHAMZTBY-GCPOEHJPSA-N syringin Chemical compound COC1=CC(\C=C\CO)=CC(OC)=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 QJVXKWHHAMZTBY-GCPOEHJPSA-N 0.000 description 1
- QJVXKWHHAMZTBY-KSXIZUIISA-N syringin Natural products COc1cc(C=CCO)cc(OC)c1O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O QJVXKWHHAMZTBY-KSXIZUIISA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- KKSDGJDHHZEWEP-SNAWJCMRSA-N trans-3-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=CC(O)=C1 KKSDGJDHHZEWEP-SNAWJCMRSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/111—Polymer of unsaturated acid or ester
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/12—Nitrogen compound containing
- Y10S430/121—Nitrogen in heterocyclic ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/124—Carbonyl compound containing
Definitions
- the constituent units (d) derived from a radical polymerizable compound having a polycyclic aliphatic group, which constitute the alkali-soluble copolymer (A), are preferably those derived from isobornyl (meth)acrylate and tricyclo[5.2.1.0 2,6 ]decanyl (meth) acrylate.
- radical polymerizable compounds employable include tricyclo[5.2.1.0 2,6 ]decanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate and tricyclo[5.2.1.0 2,6 ]decanyl (meth)acrylate. These compounds can be used singly or in combination of two or more kinds.
- Examples of the ethylenically unsaturated compounds (B) include:
- a radiation-sensitive radical polymerization initiator (C) of such a type in such an amount that when a coating film having a dry film thickness of 70 ⁇ m in an uncured state is formed, the coating film has a 365 nm radiation transmittance of not less than a specific value and a 405 nm radiation transmittance of not less than a specific value.
- the radiation-sensitive radical polymerization initiators include acylphosphine oxides, such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis-(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide; 2,2-dimethoxy-1,2-diphenylethane-1-one, benzyl dimethyl ketal, benzyl- ⁇ -methoxyethyl acetal, and 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl)oxime.
- Examples of commercial products thereof include Lucirin TPO (available from BASF Japan Ltd.) and Irgacure 651 (available from Ciba Specialty Chemicals K.K.). These compounds can be used singly or in combination of two or more kinds.
- the radiation-sensitive radical polymerization initiator is used in an amount of usually 20 to 40 parts by weight, preferably 20 to 30 parts by weight, more preferably 22 to 27 parts by weight, based on 100 parts by weight of the alkali-soluble copolymer (A).
- alkyl ethers of polyhydric alcohols such as ethylene glycol monoethyl ether and diethylene glycol monomethyl ether
- alkyl ether acetates of polyhydric alcohols such as ethyl cellosolve acetate and propylene glycol monomethyl ether acetate
- esters such as ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, ethyl 2-hydroxypropionate and ethyl lactate
- ketones such as diacetone alcohol
- thermal polymerization inhibitor can be added to the photosensitive resin film of the invention.
- thermal polymerization inhibitors include pyrogallol, benzoquinone, hydroquinone, methylene blue, tert-butyl catechol, monobenzyl ether, methylhydroquinone, amylquinone, amyloxyhydroquinone, n-butylphenol, phenol, hydroquinone monopropyl ether, 4,4'-(1-methylethylidene)bis(2-methylphenol), 4,4'-(1-methylethylidene)bis(2,6-dimethylphenol), 4,4'-[1-[4-(1-(4-hydroxyphenyl)-1-methylethyl)phenyl]ethylidene]bisphenol, 4,4',4"-ethylidenetris(2-methylphenol), 4,4',4"-ethylidenetrisphenol and 1,1,3-tris(2,5-dimethyl
- the photosensitive resin film of the invention can be added fillers, colorants, viscosity modifiers, etc., when needed.
- the photosensitive resin film of the invention is formed.
- the components are mixed to prepare a radiation-sensitive resin composition first.
- the photosensitive resin film of the invention is formed.
- the photosensitive resin composition may be applied onto a chip substrate and heated to remove the solvent, whereby a desired photosensitive resin film is formed on the chip substrate, or the photosensitive resin composition may be applied in advance onto a flexible base film and dried to form a photosensitive resin film, and the thus formed photosensitive resin film may be bonded onto a chip substrate when it is used.
- a low pressure mercury lamp, a high pressure mercury lamp, an extra-high pressure mercury lamp, a metal halide lamp, an argon gas laser or the like is employable.
- the light irradiation dose varies depending upon the type of each component in the composition, amount thereof, thickness of the coating film, etc., but in case of using, for example, a high pressure mercury lamp, the irradiation dose is in the range of 100 to 1500 mJ/cm 2 .
- the photosensitive resin film of the invention can be sufficiently cured even by the above-described light irradiation only, but depending upon the purpose, the film may be further cured by additional light irradiation (referred to as "post exposure” hereinafter) or heating.
- the post exposure can be carried out in the same manner as in the above-mentioned radiation irradiation.
- the irradiation dose is not specifically restricted, but in case of using, for example, a high pressure mercury lamp, the irradiation dose is preferably in the range of 100 to 2000 mJ/cm 2 .
- the photosensitive resin film obtained above was exposed to an ultraviolet radiation of 1000 mJ/cm 2 through a pattern mask for resolution measurement by means of an extra-high pressure mercury lamp (OSRAM HBO-1000W/D). Then, the resin film was developed with a 2.38 wt% aqueous solution of tetramethylammonium hydroxide, washed with running water and spin-dried to obtain a patterned cured film as a test specimen.
- OSRAM HBO-1000W/D extra-high pressure mercury lamp
- the test specimen was observed by a scanning electron microscope to measure a resolution.
- the "resolution” was judged by resolving a square pattern of 75 ⁇ m x 75 ⁇ m. A case where the pattern was resolved without any residual resist and an angle of the side was 85 to 95° was evaluated as "A”, and a case where the resulting image deviated from the above range was evaluated as "B".
- Adhesion to the substrate was evaluated by observing a section of the resist-cured film after development by means of a scanning electron microscope. A film in which lifting of resist was not observed at the periphery of the opening or the edge of the wafer was evaluated as "A”, and a film in which lifting of resist or peeling of resist was observed was evaluated as "B”.
- the residual film ratio was determined by measuring a film thickness after development.
- the residual film ratio is a value obtained by dividing a film thickness after development by a film thickness after prebaking and multiplying the obtained value by 100.
- a film having a residual film ratio of not less than 90% was evaluated as "A”
- a film having a residual film ratio of less than 90% was evaluated as "B”.
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Materials For Photolithography (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
- Polymerisation Methods In General (AREA)
Claims (6)
- Photosensitiver Harzfilm in einem ungehärteten Zustand, der umfasst:(A) ein alkali-lösliches Copolymer, das umfasst:(a) Bestandteilseinheiten, die von α-Methyl-p-hydroxystyrol abgeleitet sind, in Mengen von 1 bis 30 Gew.-%,(b) Bestandteilseinheiten, die von einer radikalisch polymerisierbaren Verbindung mit einer Carboxylgruppe abgeleitet sind, in Mengen von 5 bis 20 Gew.-%,(c) Bestandteilseinheiten, die von einem Acrylsäurealiphatischen-Ester abgeleitet sind, in Mengen von 20 bis 40 Gew.-%, und(d) Bestandteilseinheiten, die von einer radikalisch polymerisierbaren Verbindung mit einer polyzyklischen aliphatischen Gruppe abgleitet sind, in Mengen von 30 bis 60 Gew.-%,(B) eine Verbindung mit zumindest einer ethylenisch ungesättigten Doppelbindung, und(C) einen strahlungssensitiven Radikalpolymerisationsinitiator durch dessen Verwendung ein Beschichtungsfilm mit einer Trockenfilmdickte von 70 µm in einem ungehärteten Zustand eine Strahlungsdurchlässigkeit bei 365 nm von nicht weniger als 10% und eine Strahlungsdurchlässigkeit bei 405 nm von nicht weniger als 60% aufweist,
wobei der strahlungssensitive Radikalpolymerisationsinitiator (C) in einer Menge von 20 bis 40 Gewichtsteilen basierend auf 100 Gewichtsteilen des Bestandteils (A) enthalten ist, und eine Trockenfilmdicke des photosensitiven Harzfilms nicht weniger als 50 µm beträgt. - Photosensitiver Harzfilm nach Anspruch 1, wobei die Verbindung (B) mit zumindest einer ethylenisch ungesättigten Doppelbindung in einer Menge von 30 bis 80 Gewichtsteilen basierend auf 100 Gewichtsteilen des alkali-löslichen Copolymers (A) enthalten ist.
- Photosensitiver Harzfilm nach Anspruch 1, wobei das alkali-lösliche Copolymer (A) eine Glasübergangstemperatur von nicht geringer als 60°C aufweist.
- Photosensitiver Harzfilm nach Anspruch 1, wobei die Bestandteilseinheiten (d) die von einer radikalisch polymerisierbaren Verbindung mit einer polyzyklischen aliphatischen Gruppe abgeleitet sind, welche das alkali-lösliche Copolymer (A) aufbauen, von Isobornyl (meth) acrlyat und Tricyclo[5.2.1.02,6]dekanyl (meth) acrylat abgeleitet sind.
- Photosensitiver Harzfilm nach einem der Ansprüche 1 bis 4, wobei der strahlungssensitive Radikalpolymerisationsinitiator (C) (e) 2,2-Dimethoxy-1,2-diphenylethan-1-on und (f) 2,4,6-Trimethylbenzoyldiphenylphosphinoxid umfasst, und
das 2,2-Dimethoxy-1,2-diphenylethan-1-on (e) in einer Menge von 17 bis 30 Gewichtsteilen enthalten ist und das 2,4,6-Trimethylbenzoyldiphenylphosphinoxid (f) in einer Menge von 3 bis 10 Gewichtsteilen enthalten ist, basierend auf 100 Gewichtsteilen des alkali-löslichen Copolymers (A). - Gehärteter Film, der durch Photohärten eines photosensitiven Harzfilms in einem ungehärteten Zustand gebildet ist, wobei der photosensitive Harzfilm umfasst:(A) ein alkali-lösliches Copolymer, das umfasst:(a) Bestandteilseinheiten, die von α-methyl-p-pyroxystyrol abgeleitet sind, in Mengen von 1 bis 30 Gew.-%,(b) Bestandteilseinheiten, die von einer radikalisch polymerisierbaren Verbindung mit einer Carboxylgruppe abgeleitet sind, in Mengen von 5 bis 20 Gew.-%,(c) Bestandteilseinheiten, die von einem Acrylsäurealiphatischem-Ester abgeleitet sind, in Mengen von 20 bis 40 Gew.-%, und(d) Bestandteilseinheiten, die von einer radikalisch polymerisierbaren Verbindung mit einer polyzyklischen aliphatischen Gruppe abgleitet sind, in Mengen von 30 bis 60 Gew.-%,(B) eine Verbindung mit zumindest einer ethylenisch ungesättigten Doppelbindung, und(C) einen strahlungssensitiven Radikalpolymerisationsinitiator durch dessen Verwendung ein Beschichtungsfilm mit einer Trockenfilmdichte von 70 µm in einem ungehärteten Zustand eine Strahlungsdurchlässigkeit bei 365 nm von nicht weniger als 10% und eine Strahlungsdurchlässigkeit bei 405 nm von nicht weniger als 60% aufweist,
wobei bei dem photosensitiven Harzfilm der strahlungssensitive Radikalpolymerisationsinitiator (C) in einer Menge von 20 bis 40 Gewichtsteilen basierend auf 100 Gewichtsteilen des Bestandteils (A) enthalten ist, und eine Trockenfilmdicke des photosensitiven Harzfilms nicht weniger als 50 µm beträgt.
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JP2003098392 | 2003-04-01 | ||
JP2003098392A JP4300847B2 (ja) | 2003-04-01 | 2003-04-01 | 感光性樹脂膜およびこれからなる硬化膜 |
PCT/JP2004/004155 WO2004090637A1 (ja) | 2003-04-01 | 2004-03-25 | 感光性樹脂膜およびこれからなる硬化膜 |
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EP1610177A1 EP1610177A1 (de) | 2005-12-28 |
EP1610177A4 EP1610177A4 (de) | 2010-07-07 |
EP1610177B1 true EP1610177B1 (de) | 2011-03-09 |
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EP04723323A Expired - Lifetime EP1610177B1 (de) | 2003-04-01 | 2004-03-25 | Lichtempfindlicher harzfilm und daraus hergestellter ausgehärteter film |
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US (1) | US7214471B2 (de) |
EP (1) | EP1610177B1 (de) |
JP (1) | JP4300847B2 (de) |
KR (1) | KR101042777B1 (de) |
CN (1) | CN100589032C (de) |
DE (1) | DE602004031718D1 (de) |
TW (1) | TW200500796A (de) |
WO (1) | WO2004090637A1 (de) |
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US7927778B2 (en) * | 2004-12-29 | 2011-04-19 | Tokyo Ohka Kogyo Co., Ltd. | Chemically amplified positive photoresist composition for thick film, thick-film photoresist laminated product, manufacturing method for thick-film resist pattern, and manufacturing method for connection terminal |
WO2007026520A1 (ja) * | 2005-08-30 | 2007-03-08 | Jsr Corporation | 感放射線性樹脂組成物およびメッキ造形物の製造方法 |
WO2007029871A1 (ja) * | 2005-09-08 | 2007-03-15 | Jsr Corporation | 感放射線性樹脂組成物およびカラーフィルタ |
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JP4765974B2 (ja) * | 2006-03-30 | 2011-09-07 | Jsr株式会社 | ネガ型感放射線性樹脂組成物 |
CA2676796C (en) | 2007-01-29 | 2016-02-23 | Eisai R & D Management Co., Ltd. | Composition for treatment of undifferentiated gastric cancer |
JP5093226B2 (ja) * | 2007-03-20 | 2012-12-12 | Jsr株式会社 | 感放射線性樹脂組成物 |
TW200919085A (en) * | 2007-09-18 | 2009-05-01 | Asahi Kasei Emd Corp | Photosensitive resin composition and laminate thereof |
JP5076945B2 (ja) * | 2008-02-12 | 2012-11-21 | Jsr株式会社 | ネガ型感放射線性樹脂組成物 |
JP2011132349A (ja) * | 2009-12-24 | 2011-07-07 | Jnc Corp | インクジェット用インク |
WO2013108716A1 (ja) | 2012-01-19 | 2013-07-25 | 日産化学工業株式会社 | ネガ型感光性樹脂組成物 |
JP5968007B2 (ja) * | 2012-03-30 | 2016-08-10 | 太陽インキ製造株式会社 | 光硬化性樹脂組成物、ドライフィルムおよびプリント配線板 |
JP6315204B2 (ja) | 2012-10-02 | 2018-04-25 | 日産化学工業株式会社 | ネガ型感光性樹脂組成物 |
KR102468581B1 (ko) | 2013-10-21 | 2022-11-18 | 닛산 가가쿠 가부시키가이샤 | 네가티브형 감광성 수지 조성물 |
JP6524972B2 (ja) * | 2015-09-28 | 2019-06-05 | Jsr株式会社 | 対象物の処理方法、仮固定用組成物、半導体装置及びその製造方法 |
JP7067470B2 (ja) * | 2016-03-31 | 2022-05-16 | 昭和電工マテリアルズ株式会社 | 感光性樹脂組成物、感光性樹脂フィルム、硬化物の製造方法、積層体、及び電子部品 |
WO2017168700A1 (ja) * | 2016-03-31 | 2017-10-05 | 日立化成株式会社 | 感光性樹脂組成物、感光性樹脂フィルム、硬化物の製造方法、積層体、及び電子部品 |
JP2016139150A (ja) * | 2016-04-04 | 2016-08-04 | 太陽インキ製造株式会社 | 光硬化性樹脂組成物、ドライフィルムおよびプリント配線板 |
US20200012191A1 (en) * | 2017-03-28 | 2020-01-09 | Toray Industries, Inc. | Photosensitive resin composition, cured film, element equipped with cured film, organic el display device equipped with cured film, cured film production method, and organic el display device production method |
JP2020076945A (ja) * | 2018-09-21 | 2020-05-21 | 旭化成株式会社 | 感光性樹脂組成物 |
TWI791224B (zh) * | 2021-05-26 | 2023-02-01 | 達興材料股份有限公司 | 鹼可溶性樹脂、保護層組成物、保護層、積層體以及光阻圖案的形成方法 |
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US7214471B2 (en) | 2007-05-08 |
TWI336813B (de) | 2011-02-01 |
KR20050120771A (ko) | 2005-12-23 |
DE602004031718D1 (de) | 2011-04-21 |
WO2004090637A1 (ja) | 2004-10-21 |
KR101042777B1 (ko) | 2011-06-20 |
JP2004302389A (ja) | 2004-10-28 |
US20060210912A1 (en) | 2006-09-21 |
TW200500796A (en) | 2005-01-01 |
CN1768304A (zh) | 2006-05-03 |
CN100589032C (zh) | 2010-02-10 |
JP4300847B2 (ja) | 2009-07-22 |
EP1610177A1 (de) | 2005-12-28 |
EP1610177A4 (de) | 2010-07-07 |
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